Rikers Island is a 413-acre spot of land in the East River, home to the eponymous and notoriously violence-ridden prison complex where beatings are the most commonly noted form of expression. In 2004, a group of concerned friends formed the New York-based Prison Education Initiative (PEI), a nonprofit aimed at changing that reputation by offering meaningful education to incarcerated women. Though classes on law or hip hop at Riker’s Rose M. Singer Center drew respectable amounts of students (generally 6-20 per class), none have matched the success of the Fashion Theory course, which boasts a 30-inmate roster. It’s no college lecture hall, but PEI is betting that smallest stitches of discussion can promote creativity and identity.Chyiome handbag designer and Project Runway alum Anna Lynett Moss teaches the class, which tackles cultural identity and design process by narrowing in on provocative style and design approaches. “People with creative training are in a unique position to envision innovative alternatives to some of our deepest social problems,” she explained to Of a Kind. The designer and humanitarian—she is developing a socially—conscious accessories line with the UN–chooses talking points that range from fashion shows to magazine spreads to educate and enlighten.

Moss poked at cultural roots of design to develop the kind of creative training she feels is most effective. During one class, she examined the influence of Ghanaian wax printing on Burberry Prorsum’s Resort 2012 collection to help her students make sense of their traditions and heritage.

For another class, Moss challenged the inmates to interpret why The Row showed their Fall 2012 collection on exclusively Caucasian models. “What does it mean for my students of color not to see many icons of beauty who mirror their image?” she stated as the basis for the discussion. “Many of my students claimed they felt alienated by conventions they see in fashion advertising and on the runway.”

Edward Burtynsky‘s portfolio of surreal industrial landscapes prompted a broader look at sweatshops and mass-produced, lower-priced clothing, Moss explained to Of a Kind. “This image stood out as a reminder of what kind of conditions must exist for communities in developing nations so that we can buy sweaters for $7 from fast-fashion retailers. A new sweater shouldn’t be $7. Many of my students said they prefer purchasing clothes second-hand, which is a smart alternative.”

She selected images of Maasai women on their wedding days from the November 1999 edition of National Geographic to illustrate cultural notions of beauty. “It didn’t seem as if many of my students had conceptualized their personal standards of beauty in a larger context, so our conversation was very rich,” Moss said.

Moss’ diverse approach has visibly generated interest and participation. What remains to be seen is how well a prison sentence can incubate a creative spirit. The best indication is last year’s documentary “The World’s Most Fashionable Prison,” which showcased designer Puey Quinones mentoring prisoners competing for a chance to design pieces for a show on Project Bilibid Runway. Moss’ tutelage is more creative than competitive, but perhaps her caged wisdom can break through the same barriers.